Reaktion #78489

Reaktionsgleichung

2-[N-(4-amidinophenyl)aminomethyl]benzothiazole-5-carboxylic acid-N-phenyl-N-(2-ethoxycarbonylethyl)amide

sodium hydroxide

hydrochloric acid

→

desired compound

2-[N-(4-amidinophenyl)aminomethyl]benzothiazole-5-carboxylic acid-N-phenyl-N-(2-carboxyethyl)amide

Lösungsmittel

ethanol

dichloromethane ethanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.DISTILLATIONthe solvent was distilled off
2. 2
   SonstigeThe crude product obtained
3. 3
   Filtrationfiltered
4. 4
   Sonstigeto remove the insoluble sodium chloride
5. 5
   workup.DISTILLATIONAfter the distillation of the solvent

Vorschrift

0.45 g (0.84 mmol) of 2-[N-(4-amidinophenyl)aminomethyl]benzothiazole-5-carboxylic acid-N-phenyl-N-(2-ethoxycarbonylethyl)amide were dissolved in 15 mL of ethanol, mixed with 2 mL of 2N sodium hydroxide solution, and stirred for 4 hours at room temperature. Then the mixture was acidified with 3 mL of 2N hydrochloric acid and the solvent was distilled off. The crude product obtained was taken up in 5 mL dichloromethane/ethanol (2:1) and filtered to remove the insoluble sodium chloride. After the distillation of the solvent, the desired compound was obtained as a yellow foam. Yield: 0.26 g (67% of theory), C25H23N5O3S (473.55); Rf value: 0.47 (silica gel; methanol/5% aqueous sodium chloride=6:4); mass spectrum: (M+H)+=474.

Quelle